More than thirty years after triggering a music and lifestyle revolution, Sony has officially retired the Walkman in Japan (there is still a lone model for sale in the U.S.). A Sony engineer named Nobutoshi Kihara designed the original model for Sony co-chairman Akio Morita, who was looking for a way to listen to his favorite operas during his many hours of airplane travel. Soon the portable cassette player was sweeping the world and, of course, leading to the very devices you’re probably carrying in your pocket right now.

The Walkman and its offspring, such as the iPod, completely changed the way we experience music. And even more compelling, these devices also had a huge impact on the way we interact (or don’t interact) with each other. Before the Walkman, listening to music was quite often something we did together. Headphones and portability changed that. The very same sounds that had been a cornerstone of our social experience suddenly transformed millions of us into isolated walking zombies.

And here’s the ironic part: Three decades later, we find ourselves seeking social connections through the very devices that isolated us in the first place.

I got a Walkman when it was still called a Soundabout (I’ve been an isolated zombie early adopter since I was a kid). The first-generation version of the player actually had two headphone jacks and a button that you pressed so that your listening partner could hear you talk to them via a small built-in microphone. Using a microphone to talk to a headphoned person right next to you seemed ridiculous. Today, that feature makes perfect sense. How many times have you used a computer or phone to communicate with someone a few feet away in the next room or cubicle? But back then, people wanted no part of the dual headphone jacks. These original portable music players sequestered us and turned listening to music into a solo performance. And we wanted it that way.

Today, the more people you have listening to music, the quieter it gets.

I’ve known my wife since we were in high school. We’ve been married for more than a decade. And we’ve never once looked at each other and said, “They’re playing our song.” And after talking to a few other couples, I don’t think we’re all that unique. She has her songs. I have my songs. Our only modern equivalent to having a shared song is when one of us retweets the other.

Of course it’s not just about married couples wondering when they should dance. The Walkman introduced a thick layer of static to the music-listening experience. We suddenly needed a new way to discover the tunes our friends liked. During the pre-Walkman era, we had a simple means of finding out what our friends were listening to. We could hear it.

In the last several years, we’ve seen a dramatic reaction to this isolation. No, that reaction hasn’t been to remove our headphones. Instead, the reaction has been to use more technology in an attempt to get the old band — our friends, colleagues, etc — back together. Now, all the major music services, from LastFm and Pandora to Mog and Apple’s new Ping, enable you to share music with friends.

Most of us still listen alone, but we’re by no means disconnected. My old Walkman has been replaced by my new iPhone. Sure it plays music. But it also lets me make calls, log on to Twitter and Facebook, share photos, play games with friends and send messages through a variety of services. I’m still wearing my headphones, but now my music player comes loaded with the tools I need to claw my way back to a state of social interaction that is a virtual replication of life before I took my first walk with a Walkman.

When I was a teenager, my portable music player was a tool that I used to feel completely alone even in very public and social settings. That was before my earbuds evolved into buddy lists. Today, my portable music player makes it almost impossible for me to ever be alone.

Still I wonder if we wouldn’t be better off occasionally removing the headphones, turning off the smart phones and returning to an age when we gathered around some over-sized speakers and social networking actually meant being together.

Recent Confessions

My name is Dave Pell, internet superhero. This blog provides an addicted insider's account of what's happening to us in the era of the realtime, social web. You can read more about the site, grab the rss feed, follow me on twitter, join the Facebook page, or get email updates.